


A Little Wine, A Lotta Courage

by tieshirtblazer



Category: Glee
Genre: Boypussy, Boypussy Kurt, First Time, GKM Fill, M/M, Masturbation
Language: English
Status: Completed
Published: 2013-11-21
Updated: 2013-11-21
Packaged: 2018-01-02 05:58:58
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, Underage
Chapters: 1
Words: 3,974
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1053327
Author URL: https://archiveofourown.org/users/tieshirtblazer/pseuds/tieshirtblazer
Summary: <blockquote class="userstuff">
              <p>After a night of light drinking, Kurt works up the courage to tell Blaine his biggest secret. </p><p>(GKM fill: BP!Kurt has never touched himself, and doesn't know how. In an attempt to be a helpful friend, Blaine offers to instruct him on how to bring himself to orgasm. He soon realizes he didn't think this through properly.)</p>
            </blockquote>





	A Little Wine, A Lotta Courage

It’s midnight when Blaine and Kurt stumble back to their hotel room, after a pleasant few hours of drinking and bonding with their fellow Warblers. Taking a trip together after the school year ends is a Warbler tradition, and despite having returned to McKinley, Kurt was more than happy to join the Warblers on their trip this year. Wes had insisted on it, “once a Warbler, always a Warbler,” though Kurt suspects Blaine may have turned on his charm and done some convincing in order to secure an invitation for Kurt. It’s not like the Warblers have ever said no to Blaine, though in this case, having been given the opportunity to share a room with Blaine for one whole week, Kurt certainly isn’t complaining.

“So… how about a few more drinks?” says Blaine, leaning against the wall.

Kurt giggles. “Easy there, tiger. We can’t invade the mini-bar since we’re underage and all, and plus I think I’ve had just the right amount of red wine to leave me feeling happy and ready for cuddles.”

“Cuddles, huh?” says Blaine, perking up immediately. “I could go for cuddles. I do so enjoy them…”

“Then get into your PJs, Mister Anderson! As dashing as your summer vacation wardrobe is, cuddling is far better with soft cotton blends. Though frankly, I’m still appalled that you haven’t taken a page out of my book and invested in silk pajamas.”

“Oh Kurt, I really don’t think I could pull off silk pajamas the way you do.”

“I beg to differ, Blaine; careful observation of you has lead me to believe that you could wear a potato sack and still have the girls a’swooning.”

“Listen Kurt, we may not all be dressed like we’ve stepped off the catwalk, but let me assure you that even my sartorial tastes run higher than potato sacks!”

“Yeah, yeah, whatever you say, Blaine Warbler.”

Once they’ve both successfully changed and gotten ready for bed – Kurt agreeing, after much persuasion, to shorten his moisturizing routine – they settle into bed, seeking each other’s warmth under the covers. Kurt smiles, warm and happy, as Blaine’s arms pull him closer.

“This was fun,” says Blaine, fingers playing with the hem of Kurt’s silk pajama top. “Scale of 1 to 10: how much do you like wine?”

Kurt giggles, enjoying the occasional brush of Blaine’s fingers against his torso. “Ask me again in the morning.”

Kurt’s breath hitches as Blaine draws swirls into the sensitive skin of his belly. His expression changes, from tipsy-fond-happy to wary, nervous.

“Hey,” says Blaine, fingers stilling. “What’s wrong? Do you feel sick? Are you okay?”

“I’m fine,” says Kurt, “It’s nothing. Well, it’s something, I just… I have something I want to tell you and I… I don’t know how you’ll react.”

“Kurt,” says Blaine, sobering up immediately and pulling him closer. “You know you can tell me _anything_. I would never judge you, or hold it against you.”

“I know, it’s just… it’s something I haven’t told anyone, it’s… a part of me and I hate it and I feel like such a… a freak, or something—”

“Hey, no,” soothes Blaine. “You aren’t a freak, you are so perfectly _you_. You’re incredible, and whatever this is, if it’s a part of you, it can only serve to make you moreso.”

“Okay,” says Kurt, taking a deep breath. “Just… promise me you won’t hate me.”

“I could never,” says Blaine easily. “There isn’t even the slightest possibility of that. What is it, Kurt?”

“Well, I’m… I’m not like you. Physically. I mean, obviously that’s the case, I’m skinny and weak and… I look like a girl and— that’s not even the problem, it’s not my appearance, it’s just. I’m more… I’m more like a girl than you know.”

Kurt scrunches his eyes closed, horrified, and tries to shrink away from Blaine, who stops him immediately with a strong, reassuring hold on his waist.

“You mean… you have…”

“Down there, I’m. I have. Girl parts. A vagina. I—feel free to leave.”

“ _Kurt_ ,” says Blaine, hands finding Kurt’s face, stroking his heated cheeks, wiping at the tears that prick the corners of his eyelids. “Stop it. I’m not leaving. There’s nothing about this that makes you a freak, Kurt. It happens. It’s more common than you think it is. Kurt, look at me.”

Kurt opens his eyes and tries not to cry at the horribly earnest look on Blaine’s face.

“You’re beautiful, Kurt. Inside and out. And every single part of you, including that, is beautiful.”

“You’ve never seen it.”

“I don’t need to see it, to know.”

“Blaine…”

“Come here,” says Blaine, pulling Kurt into a tight hug. “Thank you for telling me this, for trusting me and feeling comfortable around me and… and loving me like a friend, as I love you. It means the world to me, Kurt. I’m so proud of you.”

Kurt clings to him, and laughs weakly into his shoulder. “Blaine Anderson, how are you real? I don’t know what I’ve done to deserve you.”

“Me neither. Did you wish upon a genie, perhaps? A shooting star?”

Kurt giggles, pulling away and swatting him playfully on the shoulder. “Yes, I wished for a boyfriend, and instead I got you. Never trusting a genie again!”

“Hey!” says Blaine. “I’ll have you know I am far better than any boyfriend. And I, for one, would take you over a boyfriend any day.”

“Let me get that on tape and play it back to you on the day you find someone else, Blaine.”

“There’s no one else for me,” says Blaine, smiling fondly. “Only you.”

 _Oh,_ Kurt thinks, _How I wish you meant that._

“Kurt,” says Blaine, serious, “I hope you don’t feel like you need to be tipsy in order to tell me things you find hard to say.”

“No!” says Kurt quickly, “I always knew I could trust you. I wanted to tell you, I just… needed a little courage this time.”

“You’ve always had courage, Kurt. And you’ve always had me. My loyalty, my trust, my admiration, my everything. You can tell me anything, Kurt.”

“I know. I really do know that, and of course you have all that and more from me too. But… I’ve really never told anyone about this. Only Dad knows. And Carole. I haven’t even told Finn.” Kurt scrunches up his nose, thinking. “Though that would be weird. He’d ask the most invasive questions!”

Blaine laughs. “That he would. He’d be thrilled to have someone he could freely consult on the subject of vaginas.”

Kurt grimaces. “Oh god, I can’t even imagine what sorts of things he’d want to know. ‘What’s it like?’ ‘How do I do this?’ He’d be way too excited, and let me tell you, it’s really not that exciting.”

“I wouldn’t say that, Kurt,” says Blaine, teasing, “I mean, it must be pretty exciting to be capable of multiple orgasms. Even I’m jealous!”

“Oh,” says Kurt, cheeks pinking. “Well, I wouldn’t know what that was like. I’m a virgin, Blaine, you know that!”

“Of course,” says Blaine. “So am I. I just mean… haven’t you ever masturbated?”

“Um.” Kurt bites his lip, embarrassed. “No. I’ve never really felt the need… and it’s not like I’d know how to do it, anyway.”

Blaine stares at him. “Wait, really? You’ve never touched yourself? Kurt, you’re… you’re missing out. I mean, obviously it’ll be different for you than it is for me, but orgasms are the most incredible feeling. You’ve got to try.”

Kurt blushes wildly. “Ok, sure. I guess.”

“No, Kurt! I know that look on your face; you’re just going to file this away as something that you might try one day years down the road, but have no interest in pursuing in the near future. But… we’re doing it tonight. Kurt, my dear friend, you will not be sleeping tonight until you have experienced the all-consuming pleasure of an orgasm.”

“Blaine…”

“Perhaps several! Oh man, now I’m excited. Kurt, we’re totally making this happen!”

“Blaine,” says Kurt in a strangled voice. “I appreciate your enthusiasm, but like I said – I have no idea how to make myself feel… _that_! And it’s not like you do either.”

“Well, actually,” says Blaine with a mischievous grin. “Remember how I said I dated a girl for a few months last year?”

Kurt’s eyes widened. “You didn’t…”

“Oh yes, Kurt Hummel, I certainly did! And, I’m told, I did it rather well. Some may say I am quite skilled with my fingers.” Blaine wiggles his fingers in Kurt’s face, and Kurt can’t help but burst out laughing.

“Yeah, okay Mister Anderson, I think it’s time for bed.”

“No!” Blaine’s grin disappears and is replaced by one of his painfully earnest looks, the ones that send butterflies swooping through Kurt’s stomach, that tie his insides into knots and leave him breathless.

“Kurt, I mean it. Lie down, relax. I won’t touch you, I’ll just be here, by your side. Guiding you.”

“Blaine…”

“No, this is the perfect opportunity! It won’t be weird, I promise. And god, it will be worth it, for you to realize how good you can make yourself feel.”

Kurt stays silent, lost in Blaine’s persuasive puppy-dog eyes, and finally gives the slightest nod of assent. “Fine. Just… promise me this won’t change anything. You won’t… regret this, right?”

“Kurt,” Blaine says, reaching for his hand under the bed sheets. “I could never, ever regret this. I want nothing more than to give you good things, and make you feel them for yourself. Consider this my thank-you for telling me your secret. This will only draw us closer to each other. As friends.”

“Friends,” Kurt whispers. “Okay. So, how do I start?”

 

* * *

 

“Like I said, lie down and relax.” After Kurt settles into a comfortable position, Blaine pulls the covers over him. “See, I won’t see a thing. It’ll be like I’m not even here!”

Kurt snorts. “Blaine, I really doubt I’ll be able to forget that you’re here.”

“Okay, well remember, no judgment and I’m here only to help you. Now close your eyes, and let your mind wander. Think about… things that could potentially turn you on.”

“Blaine…” whispers Kurt, blushing.

“Don’t be embarrassed. Think of… a person you find attractive, or a romantic scene in a movie, or something. Whatever gets you blushing behind closed doors! You don’t have to tell me who or what it is, but just imagine it.”

“Okay…”

Blaine lies down next to Kurt, watching his face. His eyes are closed and slowly, he begins to relax.

“Perfect,” Blaine says, and means it.  “Now, um. Unbutton your shirt. Forget I’m here! Imagine Tom Hardy is here and he totally wants you to flash him some porcelain.”

Kurt giggles and opens his eyes. “Blaine! You’re killing the mood here.”

“No way, Tom Hardy is no mood-killer! But seriously, unbutton your shirt. It’ll… make it easier.”

“How?” says Kurt, skeptical. Still, he begins to unbutton his shirt under the covers, where Blaine – to his immense disappointment – cannot see.

“Well, masturbating isn’t necessarily just touching yourself _there_ and nowhere else. It helps to kind of… let your hands wander, over your chest and stuff. Trust me.”

Kurt sighs as he finishes with the last button. “I wouldn’t be doing this if I didn’t…”

“I know,” says Blaine, smiling. He props himself up on his elbow. “Now close your eyes again. Trail your fingers lightly across your chest and stomach, around your… your nipples, your collarbone, your bellybutton, wherever.” He clears his throat, and when he speaks again his voice is just a little deeper. “Keep your touch feather-soft and teasing, like you’ve got all the time in the world to get to know your own body.”

“This feels a bit silly,” Kurt mumbles as his hand moves across his torso under the sheets.

“Do it slower. Lighter. Try different things. Like… tug at your nipples, see what that does. Imagine… it’s that special someone doing it instead.”

“Oh,” says Kurt, breath hitching.

“Yeah,” says Blaine, swallowing back a gasp. “Just like that.”

He lets Kurt keep that up for bit, tweaking his own nipples and drawing circles around his bellybutton, breathing just a little harder, a little faster. “Let me know when you’re ready to take things further.”

“I’m ready,” Kurt breathes out.

“Good,” Blaine says. Inside, he thinks _Shit shit shit shit shit_ , because _fuck_ , he himself isn’t ready, won’t ever be ready to see Kurt like this, loose-limbed with his collarbones peeking out from the top of the covers, pale and sharp and unmarred and begging for Blaine’s mouth to suckle bruises into them.

His eyes trail up the curve of Kurt’s long neck, up the slope of his jaw line to where his cheeks have just begun to flush, a reddish hue that stands out against the whiteness of his perfect skin.

“Blaine?” whispers Kurt.

“Yeah, sorry, I was just…” _Watching you, wanting you, so badly._ “… thinking about what to do next.” He shifts a little closer to Kurt, their legs barely touching. “Let your right hand trail down between your legs, but over your pajamas. Keep your touch light and teasing. Are you… are you wearing underwear?”

“No,” admits Kurt. “The silk… it’s more comfortable without anything underneath…”

“Right,” says Blaine as his brain short-circuits briefly. “Good. That’s great.” _Holy shit holy shit._ “What are you feeling right now? Good? Bad?”

“Good,” Kurt says, softly. “Definitely good. Um. Kind of… warm all over. In a good way.”

“Great. Are you comfortable? Are the covers too heavy?”

“Maybe… just the thin sheet will be enough.”

“Okay,” says Blaine, pulling back the heavy comforter. He freezes as it passes over Kurt’s wandering hands. Now he can make out the movements of every finger, can get an even better idea of what Kurt’s doing to himself. One of Kurt’s hands, the one closest to him, is still tweaking a nipple, while the other brushes over his… his _pussy_ , just like Blaine instructed.

With the heavier sheets out of the way, Blaine continues. “Now, spread your legs a little. Let your fingers slip under the waistband of your pants, over the mound, into the folds of your… Kurt, can I call it your pussy, do you… do you mind if I use that word—”

“Please,” breathes Kurt, biting his lower lip. “Call it my pussy, yeah.”

“Fuck,” mumbles Blaine as Kurt whimpers softly. “What does it feel like?”

“God, Blaine, it’s wet,” says Kurt, “So wet and warm, I’ve never—it’s never been like this.”

“Good, Kurt, that’s—” _Jesus fuck._ “That’s a good sign, that means you’re turned on and you’re ready. Get your fingers nice and slick, especially your middle finger, let it dip down into the hole, gather up more fluids.”

“Oh my god,” whispers Kurt, “I’ve never felt the actual hole, this is so weird.”

“Good-weird or bad-weird?”

“Good-weird, definitely.”

“Great, Kurt. You’re doing so well. Now pull your fingers back to where they first dipped inside the folds, feel around in that area. There’ll be this little nub, it’s called your clit, you’ll know when you find it. It’ll feel really sensitive, like—”

“Oh,” Kurt gasps. “Yeah, I— I found it. _Fuck_ , Blaine, I didn’t know it’d feel like this.”

Blaine tries not to groan, and adjusts himself in his boxers. _Fuck_. Kurt never swears, and the fact that he just did makes it very clear how much he’s losing control, submitting himself to the promise of pleasure.

“Kurt,” says Blaine, voice rough with arousal. “Don’t be alarmed, I swear this is as much touching as I’ll do, but I’m going to put a hand on your belly. It’ll… it’ll help us tell where you’re at, since when you’re close your abdominal muscles will start twitching.”

“Oh? Yeah, okay…” whines Kurt, not even opening his eyes. Normally, he would have protested, wide-eyed and embarrassed, but Kurt, right now, would say yes to anything if it helped him get closer to the edge. Blaine realizes this, and knows it would be so easy, _so easy_ to suggest taking over with his own fingers, _it’ll go faster this way, trust me. I’m gonna make you feel so good._ Blaine knows, but resists, because this is only for Kurt, and he won’t cross that line, not when Kurt’s defenses are down like this.

Blaine slides his hand onto Kurt’s torso, finding the smooth, firm skin of his stomach. He lays his palm flat against it, rubbing in soothing circles. He watches Kurt’s face, where his pink lips part at the first touch of Blaine’s hand, his eyebrows knitting together as he continues to feel his own clit.

“How do you feel, Kurt?”

“I’m—god, Blaine, it’s slippery, I’m so wet, is this normal?”

“Fuck, Kurt, yes it’s normal, you’re doing so well, I’m so proud of you.” _I want to put my mouth on you_ , thinks Blaine desperately, _Want to taste you there, lick at your juices until you’re sobbing with it, want to suck on your clit until you’re screaming my name._

Kurt’s other hand, still at his nipples, moves lower, and brushes against Blaine’s hand on his stomach. They both gasp, Kurt drawing his hand away quickly, and Blaine pressing against his belly more firmly.

“Kurt, now take your middle three fingers and start moving them in circles over your clit. Press harder against it, not too hard, but no longer feather-soft. Go at your own pace, not too fast, not to slow. Whatever feels best to you.”

Kurt’s eyebrows furrow as he begins. Blaine watches his hand move under the sheets. “Move in circles from the wrist, Kurt. Keep your arm in place, let your hand do all the work.”

“Hm? I don’t understand— Oh!” Kurt gasps when Blaine’s hand closes around his forearm, holding it steady.

“Now move from the wrist Kurt, in circles like I said. See how the rest of your arm stays in place?”

Blaine’s hand rests against Kurt’s hipbone, gripping tight onto his arm. Blaine can feel the tendons shifting beneath the skin of Kurt’s arm, can feel every single movement of his hand.

A soft moan escapes from Kurt’s lips. “Oh, oh—that feels good, yeah.”

Blaine shifts his own hips, wincing. He’s hard as a rock under his boxers, and god, he wants, he _wants_. _This is about Kurt,_ he thinks frantically, _I’m doing this for Kurt._ Now that Kurt’s got the idea, he lets go of Kurt’s arm and puts his hand back on Kurt’s stomach.

“Move your fingers faster when you’re ready. Just keep increasing the pace a little, keep thinking about whoever it is, that it’s his fingers there, touching you, touching your clit—”

“Blaine, unnghh.” Kurt’s gasping now, his head sinking further into the pillows, hair in disarray. His flush has spread from his cheeks to his ears and neck and _fuck_ , even his chest, where the sheets have slipped, revealing a single dark rosy nipple.

Kurt’s legs shift under the sheets, thighs opening up as his hand begins to move more frantically. Blaine can only imagine the soft expanse of porcelain skin on his thighs, can only bite them in his wildest dreams. He wonders who Kurt’s thinking of, if they’ll ever get to fall between his milky white thighs, pleasure his slick pussy with the patience and reverence it deserves. He himself could spend days there, kneeling, head bowed in worship; he’d bury his tongue into the soft folds and eat him out leisurely, slow and lazy.

“Keep imagining him. Imagine his fingers sliding into your hole, one, then two, then three, not to get you ready for him but just to get you nice and wet. Imagine he wants more, he kisses down your chest and stomach and then he puts his mouth on you, where your fingers are, and sucks like he… like he wants nothing more than to bring you pleasure.”

“Fuck, fuck, fuck, fuck,” whimpers Kurt, fingers moving lightning-fast against his clit. His abs tighten under Blaine’s hand, and Blaine stops with his soothing circular rubs and press against them instead, hard and firm and insistent.

Blaine drops his head next to Kurt’s, buries his nose into Kurt’s soft, sweet-smelling hair, puts his mouth a hair’s breadth away from Kurt’s ear. “Yeah, c’mon Kurt,” he murmurs, “You’re so close. You’re gonna feel so good, Kurt, I promise. Come on, baby, yeah.”

Kurt lets out a high-pitched whine, biting his lip harder. “God, Blaine, I’m close, I’m ready, I want to come, Blaine, please.” He takes his other hand, the one closest to Blaine, and raises it shakily until his fingers are resting in Blaine’s hair, gently urging Blaine’s face closer to his own.

Blaine presses his mouth against Kurt’s ear, breathing hotly into it. “You can do it, Kurt, fuck, look at you. You’re gonna come so hard, I know it. You’re perfect, Kurt. Your pussy is amazing, I’m gonna make you love it, gonna make you love your pussy so much.”

“Yeah, Blaine, I want you to—I want you—” He lets out a shocked moan. “Yes, yes, fuck, I’m—”

Blaine’s fingers press into Kurt’s abs as his muscles twitch wildly and _fuck, yes, it’s happening._ Kurt’s mouth drops open as he cries out. His hand stills, buried between his folds. His fingers curl into Blaine’s scalp.

Blaine groans and bites gently on Kurt’s earlobe. “Blaine,” Kurt whines. Out of the corner of his eye, he watches as Kurt’s hips buck wildly and Kurt’s back arches gracefully above the mattress. Kurt whimpers through the aftershocks, holding Blaine close as he presses soft kisses into Kurt’s ear, his hair.

The orgasm leaves Kurt panting, struggling to catch his breath, and his body settles boneless against the mattress.

Kurt opens his eyes. He turns his head towards Blaine and their noses brush. They stare at each other, breathing heavily.

“What did you think?” Blaine whispers.

“I think… I wish it were his fingers instead of mine.”

Blaine’s eyes widen. _Whose fingers?—Oh. Right. Mystery guy._ “Ah. Well… assuming he isn’t someone famous, maybe… one day you’ll feel what it’s like… to have his fingers there… I mean, maybe he thinks of you too! But not just during… you know… I mean, he’s an idiot if he doesn’t realize how amazing you are, and—”

“Blaine,” says Kurt, bright-eyed and smiling. “How is it you were so coherent during all of that, and _now_ you’re babbling, hm?”

Blaine stutters. “I just… huh. I guess I should stop talking.”

“Blaine, can I tell you another secret?”

“Of course!” says Blaine, smoothing out his face into his best earnest-and-attentive expression, even though he’s so hard in his boxers that it’s near impossible to function.

“That person that I was thinking of? It was _you_.”

Blaine’s world stops, for just a moment. He gapes at Kurt, struggles to form words. “Are you—are you serious?”

“One hundred percent so.”

“Jesus fuck,” says Blaine. “I um—I need a moment. Just. To sort out my. You know. I’ll just—the bathroom. I’ll go there.”

Kurt giggles. “No, idiot. Here’s what’s going to happen. I’m going to lie here by your side while you remind yourself how _your_ kind of masturbation works.”

“Uh huh.”

“And, if perhaps you feel the need to kiss me to muffle any sounds you might make, that’d be okay with me.”

“Really?”

Kurt gives Blaine a shy smile. “Really.”

“Kurt, I—I like you so much. You make me crazy.”

“I like you too, Blaine,” he says, stroking Blaine’s cheek, “Now, listen carefully. Trail your hand down your chest and into your boxers, shut up, and kiss me.”

To Kurt’s immense delight, it turns out Blaine is just as good at following instructions as he is at giving them.

**Author's Note:**

> Hi, thank you for reading! This is my first time writing smut, so I apologize if it's a total failure!
> 
> This is actually a fill of my own prompt on GKM, found here: http://glee-kink-meme.livejournal.com/45450.html?thread=60727434#t60727434 If anyone else wants to try filling it, please do!


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